title: Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines.
abstract: Radical cyclizations of cyclic ene sulfonamides provide stable bicyclic and tricyclic aldimines and ketimines in good yields. Depending on the structure of the precursor, the cyclizations occur to provide fused and spirocyclic imines with five-, six-, and seven-membered rings. The initial radical cyclization produces an α-sulfonamidoyl radical that undergoes elimination to form the imine and a phenylsulfonyl radical. In a related method, 3,4-dihydroquinolines can also be produced by radical translocation reactions of N-(2-iodophenylsulfonyl)tetrahydroiso-quinolines. In either case, very stable sulfonamides are cleaved to form imines (rather than amines) under mild reductive conditions.
authors.forename: Hanmo
authors.initials: H
authors.lastname: Zhang
authors.forename: E Ben
authors.initials: EB
authors.lastname: Hay
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Geib
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry*
chemical_list: D005609:Free Radicals; D007097:Imines; D011083:Polycyclic Compounds; D013449:Sulfonamides; D013450:Sulfones